Proactive assistant
Proactive check-ins
Caddy looks across your connected apps and texts first when there is something worth your attention.
Let Caddy check in first
I noticed your website form is getting a lot of spam submissions today. Want me to draft an email to Squarespace support asking them to help block it?
Yes please!
The problem
Important changes live across too many tools, so you often only notice them after the window to act has passed.
How Caddy helps
- Watch email, calendar, Slack, Linear, and related work surfaces for meaningful changes.
- Text you with a short explanation of what changed and why it matters.
- Suggest the next action instead of leaving you to connect the dots.
Why Caddy is different
Caddy lives in Messages, so the workflow starts where you already text. It can text first when something matters, use connected tools when you allow it, and ask for approval before sensitive actions like sending email or changing calendar details.
What the workflow looks like
- 1
Connect the tools Caddy should monitor.
- 2
Tell Caddy what kinds of changes or deadlines matter most.
- 3
Caddy checks in proactively when it finds a useful action or risk.
Texts to try
- “Text me whenever a content deadline changes”
- “Tell me when you notice something that you can automate”
- “Check in when an important follow-up looks like it is slipping”
Common scenarios
Catch forgotten follow-ups
Caddy can notice when a message, lead, or opportunity still needs a reply and text you before it slips.
Spot operational problems
When repeated events look unusual, like spam submissions or urgent support threads, Caddy can suggest a next step.
Start from the tools you already use
Proactive check-ins work best when Caddy can monitor email, calendar, tasks, and team tools for meaningful changes.
Related: Daily briefBest ways to use it
- Start with a narrow rule, then broaden once Caddy learns what you care about.
- Use proactive check-ins for calendar conflicts, urgent messages, due tasks, and unanswered threads.
- Ask Caddy to explain why it texted you if a check-in feels noisy.
Frequently asked questions
Will proactive check-ins get noisy?
Caddy only checks in on things that it thinks are important or urgent. You can start narrow and tell Caddy what was or was not useful so future check-ins match what you care about.
Can I control which apps Caddy checks?
Yes. You choose which apps are connected and can disconnect them at any time.